How to Play Cupid
by AwkwardJello
Summary: Peggy Schuyler has a fun little hobby: playing matchmaker with her friends and family… and recording them all on YouTube. Join Peggy as she drags her friends along on crazy adventures. But in the end, can Peggy use her knowledge of romance to make the biggest match of all… her crush and herself?
1. First Chapter and It's Already Gay

A/N:I decided to take a break from all the drama and tension going on in my other fic "Your Obedient Servant," and started something light and fun. This is also kinda crack lol.

* * *

(Peggy's POV)

"Alright Sally, whenever you're ready," I said.

Sally nodded, adjusting the camera one last time. "Camera rolling… action!"

"Hey guys!" I said cheerfully. "It's Peggy again, and this is How to Play Cupid! On this channel, we match people who we believe are compatible and would be perfect for each other. And when I say 'we,' I mean me and Sally. Say hello, Sally!"

My most trusted camerawoman turned the camera around and waved hi at the lens. She then turned it back around so that it was facing me again.

"So as you already know, we like to bring a perfect happily-ever-after to couples everywhere, whether it's through blind dates or something a little more… extra. Because no one wants to be forever alone." I winked at the camera. "And also because there are certain fangirls out there who really want these ships to happen. Luckily, I'm here to provide!"

"So what couple are we bringing together today, Peggy?" Sally asked. It was in the script, but I could tell she was genuinely curious.

"Well…" I said mysteriously. "I do have a certain someone in mind…"

* * *

"I am not going on another blind date," John said, crossing his arms defiantly.

"Oh come on, John," I huffed. "Please? I already told your date you would be meeting him at the bar." Which we were currently standing outside of.

John raised an eyebrow. "The bar? Really, Peggy?"

Alright, pause. This is John Laurens. I met him at Eliza's coffee shop, where we both work. John is that gay best friend everyone needs but doesn't deserve. He's super sweet, super loyal, but also super stubborn. Especially when it comes to his so far unsuccessful love life. So… I'm going to help him out.

"Yes, John, the bar. It suits you." Oh, and another thing: John drinks a lot. He's always telling me he's working on three pints of Sam Adams.

"The bar is not the best place to find love, Peggy."

"Actually, it's—" I launched into song—-"The club isn't the best place to find a lover so the bar is where I go."

Sally jumped in. "Me and my friends at the table doing shots drinking fast and then we talk slow."

John groaned. "Please don't sing that song at a time like this. Peggy, you already set me up on five different dates already, and none of them went well." He glared at me. "You even tried to set me up with Charles Lee, of all people!"

"Hey, in my defense, how was I supposed to know he was the same Charles Lee you punched in high school?" I peeked into the window. "Oh look, your date's here! Sally, make sure to zoom in on him."

"Yes, ma'am." Sally pressed her camera against the glass, while John squinted into the window. Sure enough, there was a man sitting at the bar stool I had pointed at. The man had his brown hair tied back into a neat ponytail. He turned around, not noticing the three of us at the window, and I recognized the stubble on his chin.

John gasped. "Peggy… isn't that Eliza's ex-husband?"

"I wouldn't call him that, but yeah." Alright, pause again. The guy at the bar is Alexander Hamilton. He and Eliza got together in college, and then got married. They have a son named Philip, who's currently 15 years old. Last year, Alex and Eliza got divorced, so now he's single. "His name's Alex, John. Just for future reference."

"Peggy, why are you setting me up with my boss's ex?"

I shrugged. "I thought you two would go well together. Look, he even saved you a seat like I told him!" Alex had brought a small knapsack, which he placed on the bar stool next to him.

"Perhaps I should rephrase that. Why are you setting me up with my boss's straight ex?"

"Hey, you don't know that he's straight! He could be bi, for all we know, or even gay like you!"

John looked over at Alex skeptically. "I highly doubt a gay guy would stay with a girl for 17 years and even start a family with her."

"You never know. Maybe he was just using Eliza as a beard."

"If that's the type of guy he is, I don't wanna date him."

"Okay okay, I was joking about him using my sister to look straight. But seriously, I think you two would make a cute couple. At first, I was considering setting him up with Angelica, but then I realized Angie would never go out with her sister's ex. Besides, it would be pretty awkward even if it did work out."

"So you think setting up Eliza's ex with her employee is less awkward?"

I shrugged. "A little." I looked at John pleadingly. "Please, John? Just one more date. Even if it doesn't work out, he's a really nice guy." I stuck out my bottom lip and gave him wide puppy eyes. Sally had turned the camera to John, so the entire world was basically waiting for his answer.

John bit his lip, and looked between me and the bar entrance. Me, then the bar entrance. For a moment, I was hoping it was gonna work. There's no way John can resist cute puppy eyes. But then he shook his head. "I'm still not going."

I pouted. Ugh, I was hoping it wouldn't come to this, but—

"John, if you go on this date, and it doesn't go well, then"—-I swallowed—-"then I'll take the garbage out for you when it's your turn to do it at the café. For one week."

John seemed to perk up at the offer, but then he said, "Mmm, not satisfied."

I scowled. "Fine, two weeks."

"Still not satisfied. These are my feelings we're talking about here."

"Ugh, three weeks. You happy now?"

John sighed. "Alright, I'll do it." He glanced at the bar door and took a deep breath. "Here goes nothing." Then he disappeared into the bar.

"He's gonna get a broken heart on purpose just so he won't have to do garbage duty, isn't he?" I muttered.

"Yup," Sally answered. We watched as John got closer and closer to the spot where Alex was sitting.

"Come on, Alex," I whispered. "I'm counting on you to woo that stubborn turtle for me."

(John's POV)

I'm already regretting this. Goddamnit, Peggy.

Deep breaths, John. Deep breaths. To be honest, I shouldn't be too worked up about this. Tonight, I was either going to get a boyfriend or three weeks free of garbage duty. Win-win for me. Not so much for Peggy.

I walked over to where the Alex guy was sitting, and slid into the stool next to him. The knapsack remained untouched on his other side.

I was greeted by the bartender. "Three pints of Sam Adams, please," I ordered.

"Coming right up," the bartender answered, and got to work making my drinks. Alex overheard my order and turned to me.

"Three pints? That's impressive," he said.

"Thanks, I can handle two pints, but I'm working on three," I answered.

Alex raised an eyebrow. "I feel like I've seen you before."

"Well, I do work at Eliza's coffee shop, after all."

"Ah, so that's why. John, was it?"

"Yeah, your name's Alex?"

"Alexander, but you can call me Alex." He said, and winked at me. I felt my cheeks turn pink.

"Here are your drinks," the bartender said, setting our drinks down in front of us.

"Thanks," I said. Just then, I heard a buzz in my pocket. I whipped out my phone, and saw a new text message for me.

Peggy: R you gonna tell him ur his date or wut?

How did she know— It was then that I noticed a tiny microphone attached to the collar of my shirt. No wonder Peggy insisted on choosing my outfit for me.

"You okay?" Alex asked. "You suddenly look pale."

"Oh, it's nothing," I said, trying to sound nonchalant. "Just some issues with a friend of mine," I said through gritted teeth, and shot a glare at the bar window. Alex looked too, but Peggy and Sally quickly ducked.

Buzz. What now?

Peggy: dont tell him abt me u idiot!

You: ur literally listening in on everything we say! How is this a date if we cant even hav privacy?

Peggy: im just making sure u don't screw this up, is all

Peggy: wait

Peggy: did u say u wanted privacy? [lenny face]

You deleted "Peggy" from your contacts.

Unknown: look John just pretend we arent there ok?

Unknown: John?

You: sometimes I wonder why we're still friends.

You added "AnnoyingPegleg" to your contacts.

AnnoyingPegleg: u know u love me;)

AnnoyingPegleg: speaking of love, ur dates looking at u

Oh shit, I forgot about Alex. I shot him a sheepish glance. "Sorry, I was busy texting my friend."

He smirked. "So, you done texting your friend yet?"

I sighed. "Yeah." I had given up at this point. Peggy can do whatever she wants now.

"You know, I was worried you were gonna stop paying attention to me."

My cheeks started to heat up. Was he… hitting on me?

"So uh Alex," I stammered, trying to change the subject. "What are you doing here? I didn't know lawyers got drunk."

Alex leaned his elbows on the counter, taking a sip of his beer. "Actually, I'm here to meet someone."

"Really?" I asked, pretending to be surprised.

"Yeah."

"And who is this person you're meeting?"

"I don't know. Peggy told me he's a guy."

"So you're here because of Peggy, huh?"

"Yeah." Alex traced his finger in circles on the bar countertop. "To be honest, I don't know much about the person, other than that Peggy thinks he and I will… get along."

Wow, Peggy. So vague.

"I see. So what do you expect him to be like?"

"Well, I hope he's smart, and not an ass." I chuckled. "Hopefully, he'll be able to endure my nonstop rants from time to time. And I know looks don't really reveal much about a person's personality, but I hope"—he blushed a little—-"he's cute."

"And what's your definition of cute, hm?" I asked, giving him a half-smile.

He stuttered for a moment, but then composed himself. "He would have gorgeous eyes, nice hair, and… freckles." He smirked at me. "Know anyone like that?" I was liking him more and more.

"Not a clue," I answered in as smooth a voice as I could.

His brown eyes twinkled with mischief. "How about the angel sitting next to me right now?"

If I wasn't pink before, I was red now. "I-uh—"

Alex leaned on his elbows and looked at me with his head tilted. "Aw, you're so cute when you blush. I should make that happen more often."

My face was hot, hot, hot. Alex gave me his signature smirk again, and for a moment, I forgot that this guy was some high school kid's dad. "P-please don't."

"So John, why are you here?"

I ignored the furious blush that was practically taking over my face and imitated the way he leaned on the counter, leaning slightly towards him. "Actually," I started. "I'm also here to meet someone."

His eyebrows rose. "Oh?" He smiled at me flirtatiously. "And who is this person you're meeting?"

I rocked back and forth in my seat. "I don't know much about him, but he's intelligent. He's also a bit of a flirt, but he's also really, really handsome."

He laughed. "Is he now?"

"You know, at first I thought I was going to be disappointed, but now that I've met you—" I leaned a little closer to him—-"this isn't so bad after all."

Alex was also leaning on the edge of his seat. "So it is you! For a moment, I was worried I was going to have to reject the other guy so I could get with you instead, but I guess life works out in funny ways sometimes."

I laughed. "Yes, life can do that. You're not complaining, are you?"

He shook his head. "Not one bit."

(Peggy's POV)

"Sally, status report."

"The patient has been diagnosed with cinnamon roll blushy-itis."

"And what about his partner?"

"He also has the case of the blushies, but I'm afraid he's also infected by a deadly disease that currently has no cure."

"And what's that?"

Sally grinned. "Love."

"Look, they're getting closer!" I squealed. Both John and Alex were on the edges of their stools, not quite touching each other. Yet.

The two of them were chatting, although judging by the stuff I was hearing through my headphones, it sounded more like a competition to see who could make the other blush more. And Alex was winning. I also noticed them getting increasingly drunk. Typical.

Somehow, John eyes moved over to the window, and he somehow remembered we were still there.

"Um, Alex?"

His face inches away from John's, Alex smirked at the freckled tomato. "Yes?"

"I forgot to tell you, but… Peggy's recording all this."

There was an awkward silence. Wait for it.

Alex looked at the window, and for the first time, saw us standing there with our camera pointed at his face. Then, to John's shock, Alex winked at us and kissed him right on the lips.

John gasped, hiccuped a little, and stared at his date with wide eyes. "W-what'd you do that for?! You realize Sally got that on camera, right?"

Alex shrugged. "So? I don't mind. Let the fan girls get what they want."

John turned his shocked gaze to us, and I smiled evilly at him. Ha, take that, John! Alex is on our side.

The two of them continued their conversation/flirting, though John kept shooting dirty glances at me.

"My dear Laurens, please focus on me and not the magical fairy godmother who brought us together."

John stopped paying attention to us after that. Eventually, Alex got a text message on his phone, and said something that made me froze. "My son's at a sleepover tonight. Wanna go to my place and… hang out?" His speech was slightly slurred due to the alcohol in his system.

John turned red in the face. "I…"

"Nope. Nope. This isn't happening," I muttered, getting up from my crouching position.

"What's wrong?" Sally asked.

"Rule number one of dating: never sleep with the person on your first date," I said matter-of-factly. "It may work in romance stories, but it doesn't in real life. I'm going in." Before Sally could protest, I marched right into the bar and grabbed John by the collar.

"What—" John started, but I cut him off.

"Alright Alex, we're gonna be going now. Bye."

Alex blinked. "Um, bye?" he said, still half-drunk.

John glared at me. "Peggy, what are you doing?"

I hissed into his ear, "I'm saving you from an awkward one night stand."

John opened his mouth, then gave up and sighed. "I'll see you tomorrow, Alex," he said, smiling at the other man.

"See you at the café, gorgeous," Alex said smoothly. John blushed, but nevertheless, he followed me out.

When we got outside, he glared at me. "I was actually having a good time until you came in," he huffed, the smell of alcohol still lingering in his breath.

I placed my hands on my hips. "Actually, it was going well until you almost got physical with him."

"For your information, I was going to say no. Of course doing… that on the first date isn't a good idea."

"I dunno. The look on your face said, 'yes, yes, yes!'" I shook my head. "See, this is why Alex and Eliza didn't work out. They went too fast. I mean, come on, getting married after dating for two weeks? That's way too soon." I rolled my eyes. "But Eliza was too in love to see how anything could be wrong with that."

"So, was this date a success, then?" Sally piped in, turning the camera to face John and me.

I smiled. "Oh, it was a success, alright. Cut short, but sometimes we gotta make sacrifices for the better. Don't look at me like that, John. You'll get to go on more dates with Alex in the future, and then you can do each other as much as you want." John blushed, but his happy smile was genuine.

"And you know what else this means?" I asked, smiling evilly at him. "You still have to take out the trash." He groaned. I clapped my hands. "Well, that's it for this episode of How to Play Cupid. Stay tuned for the next episode!"

"And… cut."

"Um, Peggy?"

"Yes, Sally?"

"You said at the beginning of the video, 'It's Peggy again!'"

"Yeah, so?"

"Ma'm, this is the first episode."

"..."

"Ma'm?"

"Eh, we'll fix it in the morning."

* * *

A/N:The lyrics that Peggy and Sally sang are from the song "Shape of You" by Ed Sheeran. Hope you enjoyed this fic. It only gets crazier from here...


	2. She Wants a WHAT

**Sorry I haven't updated in such a loooooong time. My homework has been multiplying tenfold lmao. But after receiving all the reviews for my fanfics over winter break, I wanted to finish this chapter in time for Christmas, so here it is! Special shoutouts to thatyeemogirl for the extra support on this particular fanfic! Merry Christmas, you beautiful chicken nuggets! And if you don't celebrate Christmas, Happy Holidays! -AwkwardJello**

 **P.S. My family literally put up our Christmas tree yesterday lmao. The ultimate procrastination.**

* * *

(Sally's POV)

Homework, done. Tidying up, done. Laundry, done. I pedaled on my bike as fast as I could. _Almost there…_

Cinnamon Roll Café. With its sunny orange awning and the cheerful window with its logo, which was a plump cinnamon bun, plastered to it. I checked my watch. 2:00 sharp. I parked my bike and hurried inside.

Ding-a-ling. The little bell above the door rang its happy little note as I stepped into the shop. Already the wonderful smell of baking hit my nose, and I breathed it in, sighing happily. The café itself was small but not claustrophobic small. More like cozy-at-home small. That was what I liked about it. It was homey, it was heaven, it was—

"Horses!" I snapped out of my daydream and realized there was an ongoing argument happening at the counter. John was positioned behind the counter, glaring at Hercules, our fellow coworker/delivery man.

"Turtles!" John shouted back at Hercules. I nervously looked around. There were only a few customers there.

"Horses!" Hercules shouted.

"Turtles!"

"Horses!"

"Turtles!"

"Um, guys?" I cautiously approached them. "Why are you yelling?"

"Oh, hi Sally!" John greeted me with a bright smile. He then pointed accusingly at Hercules. "This guy thinks horses are better than turtles! How dare he!"

"Horses are majestic creatures, so much more than a bunch o' puny reptiles!" Hercules argued. "Not sure what you see in _those_ slowpokes."

John gasped. "You take that back!" He then shouted something in French.

"What did you call me?!"

"A big horse, which is exactly what you are!"

"I can't tell if that's a compliment or an insult!"

"Sorry for the noise," I apologized to the watching customers.

One of them smiled at me. "It's okay," he answered. "We're regulars. We've gotten used to it."

"Besides," another customer added. "They're actually quite entertaining."

"Yeah, but if they ever bother you…" I trailed off when I realized someone was missing. "Hey, guys?" John and Hercules temporarily ceased their bickering and looked at me. "Where's Peggy?"

John shrugged. "Eh, she's probably just snoring in her apartment right now." He handed an apron to me. "Here's your apron. I'll stay with you until Peggy comes. She better hurry, though. _Someone's_ not in a good mood today."

Just then, there was a loud crash in the kitchen. "SHIT!"

"Oh man," Hercules muttered. "It's Shark Week, isn't it?"

There was another crash, followed by an angry stream of words that weren't exactly PG.

"Yup," John said, making the P pop. "It's… Shark Week."

"I still don't understand how that relates to Eliza being on her, er, time of the month," I said.

John patted my head as though I was a little child. "Trust me, kid. You'll understand when you learn about shark and human anatomy."

The door suddenly banged open, and Peggy walked in. "Wassup, BITCHES!" she yelled, making us all jump at the sound of her voice.

"What the hell, Peggy?!" John scolded. "You gave us a heart attack!"

Peggy ignored him and walked over to one of the café tables. She had a huge grin on her face, and laid out a large poster she had brought in with her.

"What's with the poster?" Hercules asked. "And why do you look like you're planning to murder someone for fun?"

"You see, Herc…" Peggy said, her eyes twinkling with that spark of mischief that always got me excited as well. "I have a new project."

"Ooh, really?" I said, hurrying over to the table.

"Oh, god," John muttered. "Who's the unlucky victim this time?"

Peggy smirked. "It's none other than the owner of this café." And I saw, in bright marker at the top of the poster, the words "Operation Get Eliza A Boy/Girlfriend(OGEABG)."

"What's an o-gea-buh-guh?" Hercules asked, reading the acronym. "You couldn't have thought of something a little cooler-sounding?"

"Hey, I couldn't think of anything else okay?" Peggy retorted.

John's eyes widened. "You want to set _Eliza_ up now?"

"Sure, why not? And I plan to waste no time in getting started."

"That might not be a good idea, Peggy…"

"And why not? Eliza deserves happiness too, y'know."

"Yeah, but I'm not sure now would be—"

"WHERE'S PEGGY?" Eliza yelled from the back. "I SWEAR, ONCE I GET MY HANDS ON HER—" We all winced as there was more crashing and stomping. Finally, Eliza came storming out.

Even though she was pouring smoke out of her nostrils, Eliza was really pretty. Long, black hair that was tied in a ponytail because of dress code regulations, long-lashed brown eyes, and slender, pale arms that moved about with grace. Yup, Elizabeth Schuyler was definitely someone to be jealous of. Aaaand judging by the way everyone else trembled in front of her now, someone to fear as well.

Normally, Eliza is a really nice person. But when she's on her… y'know, she becomes sort of a merciless demon.

"Um, hey Eliza," John greeted her nervously. She narrowed her eyes at him, and he gulped.

"Oh no, it's Demonliza," Hercules whispered. "Should we put up a warning sign for the customers?"

"What are you whispering about back there, Hercules?" Eliza asked, switching her sharp gaze to him.

"N-nothing!" he said quickly.

"What are you all standing around here for?" Eliza said. "Get back to work!"

"Well you see, Eliza, our shift is over, and it's Peggy and Sally's shift now," John explained.

At the mention of our names, Eliza turned to look at me. Oh man. But instead of yelling at me, her gaze softened, and she smiled warmly at me.

"Hey, Sally!" she greeted. "How's college? You did your homework already?" It was like she became a different person.

"Yeah, I did," I answered, my shoulders relaxing a bit.

"No fair," I heard Hercules mutter to John. "Why is she nice to the younger ones and not us?"

"Eliza!" Peggy cried, coming forward to give her sister a hug, but then shrinking back when Eliza gave her the demon glare.

"You, young lady, are in big trouble," Eliza growled.

"Oof, good luck, Pegs," John whispered to Peggy. He and Hercules were tiptoeing to the door.

"And where do you think _you're_ going?" Eliza demanded. The two men froze.

"Um, our shift is over," Hercules answered nervously. "So… technically, we can go?"

Eliza's eye twitched, and she sucked in a deep breath. After letting it out, she sighed. "Alright, you may go."

Hercules yanked the door open, and he and John bolted, free from Eliza's wrath. "We'll be back later!" John called over his shoulder, leaving just me, Peggy, and Eliza. And the middle-aged woman who was impatiently tapping her foot as she waited for us to take her order.

"Sally, go take care of that customer over there," Eliza instructed me kindly. "Peggy will join you shortly, after I have a nice _chat_ with her." I could see Peggy visibly sweating, by other than that, there was no sign of terror on her face. In fact, she was _smiling_.

 _Peggy really is something_ , I thought. _Man, how is she always so chill about everything?_

"And what the hell is _that_?" Eliza snapped, pointing at Peggy's poster, which was still lying on the table.

I quickly rolled up the poster. "Oh, it's just a project for my literature class," I said. Wait, I told her I did all my homework already. Oh crap.

Eliza smiled. "It's okay if you need to take the day off to do your project, Sally. Just tell me."

"No, it's okay. It wouldn't be fair to the others. I have to put in my own weight, y'know?"

Eliza smiled. "If you insist. Now, _you_ on the other hand, follow me." Eliza disappeared into the kitchen, and Peggy mouthed a grateful "Thank you" to me. I winked at her and gave her a thumbs-up. And Peggy was gone.

I took my spot behind the counter. "Hello, how may I help you? Twelve dollars." After the woman paid, I handed her the pastries she ordered. I stashed Peggy's poster behind the counter, just as a bunch of teenagers entered the shop. They ordered, I gave them food, and they sat down at one of our tables to eat. Afterwards, they left, and I went to go wipe down the table.

 _I wonder how Peggy's doing?_

* * *

(Peggy's POV)

"So… what did you wanna tell me, sis?" I asked.

Eliza glared at me, and pointed in the far corner of the storage room. "What did I tell you about cleaning up after yourself?" she growled. I looked, and gave a loud yelp. There, propped up against the wall, was my leftover Popeye chicken from two days ago. And there was a shit ton of cockroaches crawling all over it. It was the grossest thing I had ever seen, apart from the time that one kid threw up on the counter in front of me.

"Oh, um," I stammered. "Er, about that, I, uh, _may_ have forgotten to throw that out."

Eliza rolled her eyes. "Yes, for _two_ _fucking days_."

"Sorry?" I squeaked.

Eliza pinched the bridge of her nose. "Peggy, you know how sensitive I am about tidiness. And _this_ is most certainly not tidiness."

"Is there any way I can make it up to you?" The sooner I got back into Eliza's good graces, the sooner I can start my plan for getting her a significant other.

"Well, you can start by cleaning up the mess," Eliza said.

If I had a mouthful of water, I would've spit it out. "What?! How?!" I took a quick peek at the cockroaches, and just as quickly looked away. Ew, ew, ew.

Eliza shrugged. "I dunno. You figure it out." And then she just left! Yo, who does that? Leave their own sister alone with a bunch of cockroaches? That's just savage!

I sighed. Well, I did bring this on myself. _Okay, breathe, Peggy. Breathe. You can't be a proper matchmaker if you can't even face a bunch of bugs._

I stared at the roaches, trying my best not to puke or scream.

"Alright, let's do this," I told myself. I looked around. "Now, where's the bug spray at?"

* * *

After lots of spraying and gagging, I was finally able to get the dead cockroaches(and whatever was left of my precious Popeye chicken) into a garbage bag, and tossed them into the dumpster in the alleyway next to the shop.

"I'm baaack," I declared when I entered the shop again.

"Did you get all the cockroaches out?" Eliza inquired. She seemed to be in a better mood than before, though she was probably just faking it for the sake of the little children who were now munching on their cupcakes. Otherwise, she would've probably cussed me out.

Sally wrinkled her nose, while John, who had returned along with Hercules, gagged. "Cockroaches?" Sally asked.

"Yeah, I got all the nasty buggers out," I said, making sure my sister heard the annoyance in my tone.

Eliza smiled. "Wonderful. That makes my cramps a little easier to bear now."

I stuck my tongue out at her. She rolled her eyes. "Love you too, little sis." Eliza looked around the shop. "We're low on flour, so I'm going out to get some." She headed out to the door. "Be good while I'm gone," she said, wagging a warning finger at the four of us.

As soon as Eliza stepped out the door, I whipped out my phone, and started tapping on it. "John, cover for me," I instructed said person.

He narrowed his eyes at me. "What are you up to, Peggy?"

"Just checking mah YouTube channel, that's all," I said casually. "Hey look! I got two subscribers and two likes on the first video!"

"Peggy, this is your shift. You can't be on your phone," John warned. "What would Eliza say?"

"Well, _Eliza's_ not here, and since Mama Bear ain't here, I can do whatever I want," I told him, exaggerating my voice with a Southern accent. "Besides, why are _you_ back? I thought you wanted to escape the demon's wrath."

"We did," Herc said. "But she seems to be in a better mood now, so… I guess it's safe?"

"Seriously, _what_ are you doing?" John said. He marched over behind the counter.

"Oh, Peggy, I put your poster behind the counter, where you're standing." Sally came over and took out my MPPT. Master Plan Poster Thingy.

"Thanks, Sally, just what I needed." I took the poster, made sure no customers were watching, and carefully unrolled it.

"Um, Peggy?"

"Yis, John?"

"It's blank."

"No, it's not."

"Okay, other than the"—he squinted at the top of the poster—-"'OGEABG,' it's really just a blank poster."

"Not for long," I told him mysteriously. "For you see, my friends, _this_ is how I intend to retrieve a soulmate for my dear sister."

"Where did the purple marker come from—"

"Don't question it, John. Now, as I was saying"—I took the purple marker I whipped out of my pocket and scribbled a square—-"my ultimate plan…"—I carefully wrote the word out—-"is to get Eliza a Tinder account!"

Herc's eyes widened. "You plan to get Eliza a what now?!"

"A Tinder account, Helen Keller," I repeated.

"What exactly do you mean, Peggy?" John asked. "Like, what, introduce Eliza to Tinder or…?"

I shook my head. "Ugh, you guys are hopeless. I'm _getting_ her a Tinder account. As in, I'm going to make a Tinder account _for_ Eliza."

"Is that a good idea?" John questioned.

"What do you mean is it good? It's _brilliant_! You see, all I gotta do"—-I drew two circles that looked more like blobs than anything—-"is find Eliza a match on Tinder"—-I drew a smiling stick figure with long hair(Eliza) and a stick figure with a question mark on its face—-"talk to the person"—I drew speech bubbles and scribbled some random shit inside them—-"ask them out on a date, only they're gonna think _I'm_ Eliza"—I drew another speech bubble with a heart in it, and another one with the word "yes" in it—-"have them meet her somewhere, most likely the café, since that's where she is 95% of the time"—I drew a rectangle with the word "café" on it—-"and we'll let the rest unfold!" I drew a Lenny face at the end.

Herc looked skeptically at the poster. "I don't think Eliza has ever been the type to do online dating."

I whacked him on the head. "Have you been listening to anything I said? Eliza's not doing the online dating. _I_ am. So…" I whipped out my phone again. "Let's get this shit started. Sally, camera."

"Yes, ma'am!" Sally dig around inside her backpack and took out her camera. "Camera rolling, action!"

"Welcome back to another episode of 'How to Play Cupid!'" I spread out my arms grandly. "Previously, on the last episode, we matched my gay best friend John with my former brother-in-law, Alex!" I grabbed John and pulled him in front of the camera.

"Um, hi?" he greeted the camera.

"Actually, speaking of Alex, how are you guys holding up?" I asked. I was so caught up with Eliza I forgot all about my—and the fans'—favorite gay couple.

John blushed. "Well, we went on a couple more dates," he answered, rubbing the back of his neck. "He's really sweet, a bit of a flirt. But Ima give it a chance."

"Aww," we all cooed.

"Alright, now that we know _that_ was a success…" I shoved John offscreen. "...time to move on to the main attraction! Today…" I propped the poster so the audience could see it. "...we are going to find a match for my dear sister Eliza, using the wonderful app called Tinder!" I posed with the poster for 5 seconds. "Can you guys do some background audience clapping?" I whispered to Herc and John. "Y'know, for effect? So I don't look like an idiot just standing here?"

"Oh!" Herc and John started clapping. "Whoo, go Peggy!" Herc cheered.

"Yeah, go Peggy," John muttered less enthusiastically.

"Thank you, thank you. Now"—I put the poster away, and replaced it with my phone—-"we're gonna start by creating a Tinder account for Eliza." I scrolled through my apps. "Actually, I didn't even download Tinder yet, so I'm… just gonna do that now."

"Wow, I guess even Cupids procrastinate," John muttered to Hercules.

"Shut up!" I hissed at him. "Anyway, installing's gonna take a while, so… let's see who John's texting in the meantime!"

John had been texting someone, and judging by the pink blush creeping across his cheeks, I can guess who. At the mention of his name, his head whipped up. "What?! No way!" He held his phone protectively to his chest. "You are _not_ invading my privacy again!"

"Ugh, fine." I clapped my hands. "Break time, cut!"

John continued texting, and when the person sent their next text, he giggled.

"Did… you just giggle like a 12-year-old girl texting her crush?" Herc said.

The blush on John's cheeks intensified. "Sh-shut up!" he cried indignantly.

"What do you mean, Hercules? He _is_ a 12-year-old girl texting her crush," I said matter-of-factly, and swiped John's phone.

"Hey! What did I say about privacy?!"

"Relax, I'm not gonna show it to the whole world. I'm not _that_ evil." I snickered when I saw the word "Bae3" at the top of the chat, and scrolled through the messages. "Damn, the things you guys say to each other."

Sally glanced over and blushed. "Um, Peggy, should we be seeing this? These things sound a bit… graphic." One thing about Sally is that even though she loves romance and fluff just as much as I do, she can't handle anything more physical than that.

"Geez, John, it sounds more like you're friendzoning him than actually se—"John clamped his hand over my mouth and reached for his phone. "Mmmmf! Mmf mmmmf!"

"I'll take that back now!" he said angrily, his face a red tomato now.

"No way, I wanna try out some pickup lines first!"

"Give it back, Peggy!"

"Um, should we stop them?" Sally asked nervously.

"Nah, this is way too entertaining," Herc said, pulling out a bag of popcorn.

"What is all this commotion?" We all froze. The demon herself was standing in the doorway, armed with a deadly bag of groceries. "John, why do you have Peggy in a headlock?"

"Um," John stammered. "She… was invading my privacy?"

"Well, that's just Peggy. Now can you let go of her?" John released me from his iron grip.

"Now Peggy, can you please give back John's phone?"

I sighed and handed John back his phone. "Fine, _but the pickup lines…_ "

Eliza raised an eyebrow. "Pickup lines?"

"Yeah, Peggy wanted to use pickup lines on Alex on John's behalf," Sally piped up. Her eyes widened. "Oops."

"Oh boy, this is gonna be awkward," Herc muttered.

Eliza looked at John, then at me, then at John. Finally, she shrugged. "Meh, Alex already told me."

"H-he did?" John and I said in unison.

"Yeah, he called me at three in the morning and wouldn't shut up about this freckled cutie he met at the bar." Eliza pinched the bridge of her nose. "Finally, when he was done, I told him, 'Well, congratulations, Alex. I'm going back to sleep.' And I hung up." She smiled at John. "Congratulations on your new relationship, by the way. Let me know if you need any advice on how to deal with him, ok?"

"Er, okay?" John leaned in close to Eliza, and whispered. "Did he really call me cute?"

"Yes. I'd say I've heard the word at least a thousand times already."

John leaned back into the counter and clutched his heart. "He called me cute," he squealed happily.

"What a fanboy," Herc muttered.

"He's cute when he's fanboying, though," Sally giggled.

"I want a Christmas tree," Eliza said suddenly. We all turned to look at her.

"Um, what?" Herc asked.

"I want. A Christmas tree," Eliza repeated slowly.

"But why? The school year didn't even start yet. And aren't you supposed to be craving food, not holidays?"

"I said I want a Christmas tree," Eliza growled, her demon voice back.

"Okay, yes ma'am!" We all rushed to retrieve the Christmas tree from the back.

"Why a Christmas tree, though?" Sally asked.

"Don't question it," John warned.

* * *

 **Once again, thank you so much for all the support, it really does mean a lot to me. I wouldn't have gotten this far on Fanfiction if it wasn't for you guys, so thank you sososoosososo much! Merry Christmas and a Happy New Year!**


	3. Let's Get This Lams

**I'm gonna start coming up with funny titles for these chapters.**

* * *

(Peggy's POV)

"Hello, we are back!" I declared to the camera two days after the last chapter. "So I got the Tinder app, and we're gonna get started with finding a date for my sister!"

"You seriously forgot for _two days_ before you finally remembered your Tinder plan," John muttered. "Talk about a terrible Cupid."

"Sally, make sure to edit that out of the video."

"Yes, ma'am!"

"Really?" John said.

I glared at him. "Yes, and for your information, I didn't _forget_. I was simply _waiting_ for the perfect time to do this behind Eliza's back."

"For two days?"

"Hey, a matchmaker's gotta be extra stealthy if she's gonna do her job right." I turned back to my phone. "Now, where was I? Oh right, this terms and agreements shit I have to accept." I clicked "Accept" without looking at it for a second longer. Let's be honest, no one reads those. (Lol I dunno if Tinder has that kind of thing but every app that I've ever used has it so…) "Ah, we need to log in with our Facebook. Luckily…"

I shot a nasty grin at the camera. "Because Eliza is so trusting and kind, she tells me all her passwords." I punched in Eliza's Facebook password and bam! We're in.

"Eliza trusts you with her passwords?" John asked. "I don't even trust you with my sandwich."

"But you said I could try it!"

"I said you could take a _nibble_ out of it. Instead, you bit off, like, half of it off!"

"Aaaanyway, back to Tinder. Let's see. What gender do we prefer? Eliza's pan, so I'd say both male and female. Age range? Somewhere around 40 years old. I don't think Eliza's a pedo. What should we put in our profile? Hmm, how about…" I started typing. "'Hi, my name is Elizabeth Schuyler, but I go by Eliza."

"Looks pretty normal so far," Herc commented carefully. "Where's the twist?"

"'I'm the proud owner of a small coffee shop called the Cinnamon Roll Café,'" I continued typing. "'But I can be a total sinnamon roll when it comes to bed. Winky face winky face. P.S. I also have a teenage son named Philip, but don't worry, he doesn't bite. I like flowers, little kids, setting stuff on fire whenever I'm pissed off, kittens, and'"—I snickered—-"'tits.'"

John spat out the mouthful of water he was drinking. "EXCUSE ME WHAT?!"

"Ooh, maybe instead of 'I go by Eliza' I could say…" I grinned as I typed out the next words. "'Roses are red, high school depression is blue, you can call me Eliza if you are my boo!' Pretty cute, huh?"

"Yeah, especially that second line," Herc snickered.

"We gotta include a profile picture, huh? Lemme see." I scrolled through all my photos, until I got to one of Eliza standing before a colorful garden, her white teeth showing in her smile. "Mm, nah." I looked at a photo of Eliza at her thirty-god-knows-how-old birthday, laughing in the soft light of the candles. "Nah." I saw one of Eliza at the beach, building a sandcastle with Philip when he was ten. "Cute, but not what I'm looking for." Finally I got to a random picture I took of Eliza sneezing. "Oh, _this_ is the one, alright!"

John looked horrified. "Why are you going with that one? Go back to the other pictures!"

"I'm just kidding! This one is the winner." I turned back the garden photo. "And now for the fun part! Dayum, look at all these babes!" I swiped right on the first three. "Ooh, they all gonna have competition! Ew, I don't like this one." I swiped left on the next picture.

"He looked pretty cute," John retorted.

"Nah, he looks like one of those movie characters who looks sweet at first but turns out to be some creepy stalker."

"How can you even tell—you know what, I'm not even questioning you anymore."

"Ooh, this one looks promising. Nah, that one gives me playboy vibes. Eh, this one will probably catfish Eliza faster than you can rap 'Guns and Ships.' Aw, this guy got glasses. Ima swipe right on him! Oh my Miranda, this guy has a puppy! Keeper! This chick is a soccer player, but the real question is: is Eliza into sports? Mm, no. Ooh, _this_ chick is also posed in front of a garden. Right!" I swiped left and right until I got to a particular photo of a woman. "Hmm, this is gonna be tough."

Sally peeked over the camera. "She looks nice," she said.

I nodded. "Oh, that rack is looking _fine_ , I tell you."

John looked disgusted. "Are you seriously commenting on a girl's chest size now?"

"Hey, I'm not done yet. Even though it's obvious she's buxom, she's still wearing a sweater, so it shows modesty of some sort. Definitely Eliza's type."

"Or she's just cold," John muttered.

"But?" Herc asked.

"But look!" I pointed at the little girl next to the woman. "She has a daughter. Or a niece. You never know. My point is, is it alright if Eliza's significant other already has a child? Actually, who am I kidding, Eliza loves kids. She'll win over that little girl's heart in no time. Right!" I stood up straight, and spoke to the camera. "You know what, we have enough contestants for our dear Eliza, so that's gonna be it for today. Stay tuned for the next video! Once again, this is Peggy on How to Play Cupid, signing out!" I did a small salute. "Cut!"

I grinned at the rest of the café peeps. "Whoo, I feel accomplished! How 'bout the four of us go get a drink tonight, to celebrate? It's all on me!"

"Um, Peggy," Sally said nervously. "I'm not of legal drinking age."

"I have a nice supply of fake IDs at home."

"No way is Sally going," John said defiantly.

"Ugh, fine. Be a goody-two-shoes, why don't you. Then I guess we'll just invite Alex along. Haven't seen him in a while."

"Don't! He's probably busy working at the law firm—" John started.

"Too late, Johnny boy. Already dialed his number." I waited for the guy to pick up. "Hey, Alex! You wanna go for a drink tonight? What, you busy?" John gave me a "I told you so" look. "Aw, that's a shame"—I smirked at John—-"because your _boyfriend's_ gonna be there. What's that? Great! See ya at 6!" I hung up. "Your dear Alexander is coming with us. Looks like he misses you," I singsonged.

John blushed an adorable pink, and didn't say anything else. "Fine, but I'm not having another drinking competition with you."

 _Three hours later…_

(Alex's POV)

"Ha!" John bellowed. "Looks like Margarita had too many margaritas!" He slammed his latest glass on the bar counter.

"What are you talking about?" Peggy slurred. "I'm on my fiiiiifth glasss." She hiccuped and chugged another glass. "I doubt you're—hic—even on the third one."

"Actuuually—hic—I'm on my—-hic—seeventh. Suck it!"

"They're both wasted, aren't they?" Herc muttered.

I nodded, taking note of how flushed both their faces were. "Yes, very wasted."

"Bringing then both here was a bad idea."

"Agreed."

"Aaleeeex," John said, coming over to me and flopping down on my lap. "Coome dance with meee." He grinned his stupidly adorable goofy smile.

"Yees," Peggy chimed in. "Goo daance with him. Make my dreams come tru-u-ue."

"Babe," I said, lifting John's chin up. "As much as I want to dance with you, I think it's time we go home."

"Yeah, dude," Herc said. "You had too much to drink." He glared at Peggy. "The same goes for you."

John pouted. "Aaaaw, pretty pweez?" He stuck out his bottom lip.

"Yeah!" Peggy cheered. Herc was already picking her up off her stool. "Dance with him! Make my ship float on the Caribbean sea!" She started giggling maniacally after that.

I sighed. How could I say no to that face? "Fine, one dance. Then we're leaving."

John pulled me off my stool, and led me to the dance floor. "Yippee!" he giggled like a little kid. God, my boyfriend's gonna be the death of me.

A few hours later, we arrived at my apartment. I had to give Peggy a piggyback ride, while Herc did the same for John.

John flopped down on my couch facefirst when we got back, drunkenly commenting on how it smelled nice. Peggy ran to the bathroom, probably to throw up.

"Maybe I should stay here with you," Herc pondered. "Obviously, Peggy can't go home by herself, not in this state. And John, well, he's not going anywhere either. It will probably be hard taking care of two drunks at the same time."

I shook my head. "Nah, I can manage. You can go home, Herc. I can take care of these two."

Something dawned on Herc. "Wait, what about your son? Oh man, maybe they should stay at my place."

"Philip is staying with Eliza tonight. You know, the whole switching between divorced parents thing."

"Ohh. Well, call me if you— oh my god, what is Peggy doing?!" He and I ran over to the bathroom. To our absolute horror, Peggy had one foot in the toilet bowl, and was trying to flush herself down the toilet.

"Peggy! What in the name of Daveed are you doing?!" I cried.

Peggy looked up at us, her eyebrows scrunched up in annoyance. "I'm going to Narnia," she deadpanned.

"Aren't you supposed to go in a wardrobe?" Herc asked. "Ugh, never mind. Doesn't even matter."

"Get out of there!" I wrapped both my arms around her waist and attempted to pull her out.

Peggy wriggled around in my grasp. "I'm going to Narnia and you can't stop me!" she shouted in a drunken stupor, splashing around the toilet water.

"Herc, a little help here?"

With Herculean (ha!) strength, Hercules hoisted Peggy out of the toilet. "Unhand me, fiend!" Peggy yelled.

"Fiend?" Herc cringed, and he half-dragged, half-carried Peggy to the living room. "Hey, hey, hey! Where you going?" He stopped Peggy from running back to the toilet. The girl scowled and reluctantly marched over to the couch.

"Move over!" She shoved John, who let out an undignified yelp, off the couch and plopped onto the couch herself. "My couchie!"

John glared at her. "Gimme back my couchie senpai!" he cried, and the two of them started a ridiculous kitty fight, swatting at each other like little kids.

"You would think that John would be the more mature one," Hercules commented. "But nope. As soon as you give him a bottle of whiskey, his maturity level gets reduced to a 5. Peggy, her maturity level doesn't change at all, drunk or sober."

"I gotta admit, they're kinda adorable when they're like this," I chuckled.

"I know you're only talking about John."

My cheeks turned pink. "Ok, ok, you got me there."

"Say, have you told Philip yet, that you and John are"—he made a vague gesture in the air—-"together?"

My eyes widened. "Holy shit, I didn't. I was waiting for a good time to tell him, but I guess it never came."

Hercules shook his head. "First Eliza, and now Philip. You guys need to practice communication more." He looked concernedly at John. "Does Philip even know who John is?"

"I mean, his mom owns the coffee shop where John works, so yeah, Pip's seen him from time to time, but they never actually talked."

Herc breathed a sigh of relief. "Well, at least John won't be a complete stranger to the kid." He made his way to the door. "You sure you'll be okay on your own?"

"Yeah, don't worry. Thanks for the help, Herc."

"No problem. Call me if you need anything."

"I will. Bye."

Right when Herc closed the door, Peggy _had_ to throw up all over John. John, who didn't seem to notice the vomit covering the front of his shirt, lumbered over to me.

"Alex," he slurred. "Let's go to bed." He leaned against me, and I was practically staggering under his weight.

"Oh yeah, baby!" Peggy giggled as I dragged John toward my room. "You go get that action!" Then she started singing, offkey, "John and Alex sitting in a tree, F-U-C-K-I-N-G. First comes love, then comes the bed, then comes the day you say 'I do' and wed!" She laughed at her little song.

"Har har, very funny," I drawled. I was able to sit John on the edge of my bed, before he fell backwards with a flump. "Alright, don't take this the wrong way, but I'm gonna have to undress you, so you don't wake up with Peggy vomit all over you."

"My shipping sensors are tingling!" Peggy yelled from the living room.

I ignored her and carefully moved to unbutton John's shirt. "Easy, easy," I murmured, more to myself than to my boyfriend. I finally undid all the buttons. "Alright, babe, I'm gonna need you to sit up so I can get it off you."

John winked at me, making my heart lodge into my throat. "Anything for you, handsome." Sober John would've never said that.

Slowly, he moved to a sitting position, and slowly, I slid his button-down off. Thank goodness Hercules used his top-notch fashion sense to convince John to wear a button-down. He looks pretty good in it.

No sooner did I drop the wet, sopping shirt on the floor did a pair of strong arms wrap around my waist and pull me down with them.

"J-John?"

He stared intensely at me, and I could see the pink of his cheeks deepen. "Alex…" His hands ran up and down my back("I smell that increasing sexual tension!" Peggy called).

"Y-yes, John?" _Unholy shit, I'm straddling him._

He brought his face closer to mine, until we were less than an inch apart. I could smell the margaritas in his breath. "Alex… sleep with me." And then he passed out. His arms fell limp at his sides, no longer holding me.

And just like that, things went from 0 to 100 and then back to 0.

Still blushing furiously, I crawled off of John, and picked up his shirt. Then I went to put it in the laundry machine. When I checked on Peggy, she was fast asleep, with the stupidest grin on her face. It was like she knew what was up. To be honest, I wouldn't put it past her if she did.

I made myself a sandwich for dinner, brushed my teeth, checked on Peggy one last time(she was snoring), and went to bed. I tucked John under the blanket, then pondered if I should snuggle next to him. Not wanting to disturb his privacy, and because the couch was already occupied by Peggy, I thought about taking Philip's room for tonight. But then I would be disturbing _Philip's_ privacy. So I just went with sleeping on the floor instead.

"G'night, John," I whispered, and kissed his forehead. Then I got out a second blanket and struggled to fall asleep on the cold, hard floor.

 _The next morning…_

(Philip's POV - yass my boy Philip is finally here!)

"Bye, Mom," I said as I got out of the car.

Mom smiled and waved. "Bye, Philip." She blew a kiss. "Love you, hon."

I laughed. "Love you too, Mom." She waited until I was inside the apartment before she drove away. I made my way up the stairs, and then walked down the hall until I got to Apartment 1776.

I unlocked the door with my keys, and stepped inside. Pops was already cooking something, probably scrambled eggs, for breakfast. He looked up upon hearing the door open.

"Hey, Pip!" he greeted, waving at me over his shoulder.

"Morning, Pops," I greeted him back. That was when I noticed Aunt Peggy lying on the couch. "Um, Pops, what's Aunt Peggy doing here on our couch?"

Pops turned around and jumped, as though he was seeing Aunt Peggy for the first time. "Oh, she had a drink last night and passed out," he explained.

I frowned. "Is she gonna be okay?"

"Yeah, she just needs to sober, but she'll be fine."

"Alright, I'm going to my room, ok?"

"Wait, Philip, before you go, there's something I need to—"

But it was too late. As I was making my way to my room, I saw that Pops' door was halfway ajar. And then what I saw inside scared me so much I let out a loud girly scream that startled Aunt Peggy awake.

"POPS, WHY IS THERE A HALF-NAKED MAN IN YOUR ROOM?!"


End file.
